CHEBI:77822 - dextilidine

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ChEBI Name dextilidine
ChEBI ID CHEBI:77822
Definition An ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has S configuration at the carbon bearing the phenyl group and R configuration at the carbon bearing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, ent-dextilidine. A prodrug, tilidine is converted by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1S,2R) isomer (i.e. the isomer derived from dextilidine).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H23NO2
Net Charge 0
Average Mass 273.37000
Monoisotopic Mass 273.173
InChI InChI=1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3/t15-,17+/m1/s1
InChIKey WDEFBBTXULIOBB-WBVHZDCISA-N
SMILES CCOC(=O)[C@@]1(CCC=C[C@H]1N(C)C)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
Application(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dextilidine (CHEBI:77822) has role opioid analgesic (CHEBI:35482)
dextilidine (CHEBI:77822) has role prodrug (CHEBI:50266)
dextilidine (CHEBI:77822) is a ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate (CHEBI:77817)
dextilidine (CHEBI:77822) is enantiomer of ent-dextilidine (CHEBI:77821)
Incoming tilidine (CHEBI:77823) has part dextilidine (CHEBI:77822)
ent-dextilidine (CHEBI:77821) is enantiomer of dextilidine (CHEBI:77822)
IUPAC Name
ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
INNs Sources
dextilidina WHO MedNet
dextilidine WHO MedNet
dextilidine WHO MedNet
dextilidinum WHO MedNet
Synonyms Sources
(+)-(1S,2R)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate ChemIDplus
(+)-ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylate ChemIDplus
(1S,2R)-(+)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate ChEBI
Registry Number Type Source
32447-90-8 CAS Registry Number ChemIDplus
Last Modified
20 March 2014